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Making a pact with a demon

Now I've bumped into a rather juicy situation as a DM. See, one of my players wants to make a pact with a demon. Reason? She is bound by a secrecy sigil, a tattoo that prevents her from speaking about a specific (very VERY) important topic. I have established in this homebrew world that demons can shatter these sigils.

So now I get to play the part of a cunning demon who wants to trick her into agreeing to something very favorable for said demon. I've got some ideas on the nature of the pact, but I'd like to hear the community's ideas on the topic. How would YOU handle this situation, what terms should the demon go for, and what "tricks" would you try to pull off? My campaign is Pathfinder, though I can see how this could leak into other editions.

In every edition of D&D that I'm aware of, demons seek to spread disorder and despair. Therefore, the terms should seek bring about that state of affairs. Ideally, the outcome should be one that makes the player question whether this deal was worth it. In particular, a deal that seems understandable and barely worth it at the moment it's made becomes one in which hidden costs are revealed over time, making the value of the deal more and more questionable.

The obvious way to achieve this is one where her ability to speak about this topic causes an unwelcome turn of events. In other words, the situation would have turned out better if she'd been compelled to maintain her silence in the first place. Therefore, the demon benefits twice: once from whatever she promised in her pact, and again because the "benefit" she got only made things worse.

There may be other ways to go about this, but it seems to me that there are two general paths to follow, assuming your demons are like mine. The first is where the character's actions cause disorder and despair to the environment. In this case, the cost depends how guilty the character feels about her actions, but doesn't necessarily impact the character herself. This could be a path to the eventual corruption and "fall from grace" of the character. The other path is one where the personal chaos and unhappiness of the character is increased, which is more direct and obvious in its costs.

One overall consideration is whether this is the "correct" or "incorrect" choice on the player's part. If it is "correct," the player should be rewarded (in terms of interest or benefit) regardless of what happens to the character. If it is "incorrect," it's the player who should regret their choice. However, in either case, you should bear in mind that you do not necessarily want to inflict despair on your own player. This, as in all in-game activities from my point of view, is to increase the engagement or overall enjoyment of the game as a whole. I would hope that the point of the exercise isn't to lose the player.

Edition doesn't matter with this one... it's the same across the board and is "editionless".

Are your demons similar to Earthly mythology and general D&D mythology, where they are ruthless, vain and greedy, willing to do ANYTHING to get ahead (and "get ahead" means getting souls)?? If so, this could be easy.

There are two ways to go about this - "Dickish" and "Sneaky".

If you want to DM like a jerk, just have the pact say, "I will erase this tattoo for you because it pleases me to do so. I will do this in return for your soul." If she bites and accepts, then there's a choice. Kill her then and have the demon destroy the tattoo as her lifeless body lies there... OR let her live her life for the next XXX years and as she dies of old age, the demon would show up and destroy the tattoo. This is the EASY way to do it.

If you want to be SNEAKY, then it's a bit harder.

How about a mission... the Paladin's of Pelanor are being a pain to him, so he wants the entire order destroyed. When she's done with that, he'll take off the tat. Like you said, he wins twice. This may cause major havoc for her if she is any sort of lawful or non-chaotic-good. (CG folks could rationalize it as serving the GREATER GOOD) Or, provide a bunch of souls for the demon - pervert an orphanage or convent/monastery and turn them all into demon worshipers!!

And don't forget the actual removal of the tat. Unless she is VERY anal about wording, she may not list the CONDITIONS for removal/destruction. A 500d6 lightning bolt will remove it!!! Ripping off the arm will remove it!! Going through her chest to rip it off her back will remove it!

The options are about endless!!

In prior groups I've played with, when we got bored/burnt out, we would sit around and try to corrupt wishes for days at a time... "I wish I had a magic sword!" "You do - embedded in your skull!" You do - being carried by it's present wielder, Conan!" You do - but it's located on another plane!" When playing silly games like this, it is VERY easy to twist words around to your advantage.